Steep Mission

Climbing Heartbreak Hill to drop weight—fast.

A month or so before my wedding last year, I discovered I lived a mile away from Heartbreak Hill, and I needed to get in shape-quickly. So I decided to run up it, for 30 days in a row.

Day 1: The hill seems endless, and I'm only walking down it. A Boston Athletic Association spokesman tells me Heartbreak is a 600-meter uphill stretch, but I can't quite figure out where the start is, and after 10 minutes running up the Newton Hills, I'm huffing and puffing, and a man in a red pickup truck pulls alongside me and shouts, "Hey, you want a ride?"

Day 2: I meet a man who's done Boston 17 times and coaches with the Heartbreak Hill Striders who says the hill includes 100 meters before Grant Avenue, starting at Westbourne Road, making it close to 700 meters. I'm up in 3:30.

Day 8: I run one to three miles a day, including Heartbreak, usually at the end. Two friends come to town for my bachelor party, and I rope them into running with me. Amir takes off in a sprint. Trey hangs back, but I hear him closing in as I fade near the top. We finish in 3:15, a "Hill PR" for me. Amir works out a calf cramp the entire walk home.

Day 15: Today I try on my wedding suit. I fit into size 36 trousers, but they're snug. "Do you want me to let them out?" the tailor asks. "No," I say, determined (and a little scared).

Day 26: My goal is to run up the hill once as hard as I can, then try to break 3:30 for two more. I make it up the first time in 2:54-a Hill PR! I run the second in 3:19. That pace, stretched out over the entire 26.2 miles, wouldn't qualify me for the marathon. I lose my dinner at the top. The third hill is 3:19. The numbers mean nothing to anyone but me, but I'm thrilled (if queasy).

Day 27: Time to pick up my suit, nine days before the wedding. The size 36 fits. I've dropped 8.5 pounds. I go home and celebrate with-what else?-a run up Heartbreak.

Day 30: Today, I start my run on Heartbreak Hill and jog to downtown Boston-the last few miles of the marathon route. I think, The real Heartbreak isn't a steep piece of road in Newton. It's an experience you earn from racing the 20 miles before it, which I hope to do someday. Six days later, I get married, with no mention of Heartbreak.